1-15. (canceled)
16. A method for combating phytopathogenic fungi comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of a composition comprising a compound of the formula I
wherein:
R1 is selected from the group consisting of C2-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl;
wherein the aliphatic groups R1 are unsubstituted or carry 1, 2, 3 or 4 CN substituents;
wherein the cycloalkyl moieties of R1 are unsubstituted or carry 1, 2, 3 or up to the maximum number of identical or different groups Rb which independently of one another are selected from:
Rb is selected from the group consisting of halogen, CN, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy;
or an N-oxide or an agriculturally acceptable salt thereof.
17. The method of claim 16, wherein R1 is C2-C6-alkyl, C2-C6-alkenyl or C2-C6-alk-1-ynyl.
18. The method of claim 17, wherein R1 is C2-C4-alkyl.
19. The method of claim 16, wherein R1 is C2-C6-alkenyl or C2-C6-alk-1-ynyl.
20. The method of claim 16, wherein R1 is C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl.
21. The method of claim 16, wherein R1 is selected from the group consisting of ethyl, n-propyl, isopropyl, n-butyl, tert.-butyl, allyl, ethynyl, prop-1-ynyl; but-1-ynyl, cyclopropyl and cyclopropylmethyl.
22. A method for protecting plant propagation material and seedlings’ roots and shoots from infestation by harmful fungi comprising contacting the plant propagation material with a composition comprising a compound of claim 16.
23. A seed coated with at least one compound of formula I as defined in claim 16, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
24. A compound of formula I
wherein:
R1 is selected from the group consisting of C2-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl;
wherein the aliphatic groups R1 are unsubstituted or carry 1, 2, 3 or 4 CN substituents;
wherein the cycloalkyl moieties of R1 are unsubstituted or carry 1, 2, 3 or up to the maximum number of identical or different groups Rb which independently of one another are selected from:
Rb is selected from the group consisting of halogen, CN, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy;
or an N-oxide or an agriculturally acceptable salt thereof,
except for 2-2-chloro-4-(4-chloro-phenoxy)-phenyl-1-1,2,4triazol-1-yl-pent-4-yn-2-ol.
25. The compound of claim 20, wherein R1 is C2-C6-alkyl, C2-C6-alkenyl or C2-C6-alk-1-ynyl.
26. The compound of claim 21, wherein R1 is C2-C4-alkyl.
27. The compound of claim 20, wherein R1 is C2-C6-alkenyl or C2-C6-alk-1-ynyl.
28. The compound of claim 20, wherein R1 is C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl.
29. The compound of claim 20, wherein R1 is selected from the group consisting of ethyl, n-propyl, isopropyl, n-butyl, tert.-butyl, allyl, ethynyl, prop-1-ynyl; but-1-ynyl, cyclopropyl and cyclopropylmethyl.
30. A process for preparing the compound of claim 20, comprising reacting a compound of formula III
wherein Y is F or Cl,
with 4-chlorophenole of formula II
under basic conditions;
and reacting the resulting compound of formula IV
in the presence of a catalyst with isopropylmagnesium bromide followed by a reaction with acetyl chloride;
halogenating the resulting compound of formula V
with bromine;
reacting the resulting compound of formula VI
under basic conditions with 1H-1,2,4-triazole;
and reacting the resulting compound of formula VII
with a compound of formula VIII R1-M,
wherein R1 is selected from the group consisting of C2-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl;
wherein the aliphatic groups R1 are unsubstituted or carry 1, 2, 3 or 4 CN substituents;
wherein the cycloalkyl moieties of R1 are unsubstituted or carry 1, 2, 3 or up to the maximum number of identical or different groups Rb which independently of one another are selected from:
Rb is selected from the group consisting of halogen, CN, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy
and M is selected from the group consisting of MgBr, MgCl, Li and Na, to obtain compounds I.
31. A process for preparing the compound of claim 20, comprising reacting a compound of formula III
wherein Y is F or Cl,
in presence of a catalyst with isopropylmagnesium halide followed by a reaction with a compound of formula IX R1\u2014COCl,
wherein R1 is selected from the group consisting of C2-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl;
wherein the aliphatic groups R1 are unsubstituted or carry 1, 2, 3 or 4 CN substituents;
wherein the cycloalkyl moieties of R1 are unsubstituted or carry 1, 2, 3 or up to the maximum number of identical or different groups Rb which independently of one another are selected from:
Rb is selected from the group consisting of halogen, CN, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy;
and the N-oxides and the agriculturally acceptable salts thereof,
converting the resulting compound of formula X
wherein Y is F or Cl;
under basic conditions with 4-chlorophenole of formula II
and reacting the resulting compound of formula Va
with trimethylsulf(ox)onium halide;
and reacting the resulting compound of formula XI
under basic conditions with 1H-1,2,4-triazole,
to obtain compounds of formula I.
32. A compound of formula XI
wherein R1 is C2-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl;
wherein the aliphatic groups R1 are unsubstituted or carry 1, 2, 3 or 4 CN substituents;
wherein the cycloalkyl moieties of R1 are unsubstituted or carry 1, 2, 3 or up to the maximum number of identical or different groups Rb which independently of one another are selected from:
Rb is selected from the group consisting of halogen, CN, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy.
33. An agrochemical composition wherein said composition comprises an auxiliary and at least one compound of formula I, as defined in claim 20, an N-oxide or an agriculturally acceptable salt thereof.
34. The composition of claim 29, further comprising an additional active compound.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A method for obtaining site-specific recombination in a eukaryotic cell, the method comprising:
a. providing the eukaryotic cell
wherein
the eukaryotic cell comprises a polynucleotide that encodes a prokaryotic Bxb1 recombinase polypeptide,
wherein
the eukaryotic cell comprises a first site-specific recombination site and a second site-specific recombination site, wherein the first site-specific recombination site is a substrate for recombination with the second site-specific recombination site; and
b. contacting the first site-specific recombination site and second site-specific recombination site with a prokaryotic Bxb1 recombinase polypeptide, resulting in recombination between the first site-specific recombination site and second site-specific recombination site. The method of claim 1, wherein the eukaryotic cell is a plant cell.
2. The method of claim 1, wherein the eukaryotic cell is a yeast cell.
3. The method of claim 1, wherein the eukaryotic cell is an animal cell.
4. The method of claim 1, wherein the polynucleotide that encodes the prokaryotic Bxb1 recombinase polypeptide comprises SEQ ID NO:1.
5. The method of claim 1, wherein the polynucleotide that encodes the prokaryotic Bxb1 recombinase polypeptide encodes a recombinase polypeptide comprising SEQ ID NO:2.
6. The method of claim 1, wherein the prokaryotic Bxb1 recombinase polypeptide causes a site-specific excision of DNA,
wherein
the excision of the DNA is a result of recombination between the first site-specific recombination site and the second site-specific recombination site, and
wherein
the DNA that is excised is located between the first site-specific recombination site and the second site-specific recombination site on the same DNA molecule.
7. The method of claim 1, wherein the prokaryotic Bxb1 recombinase polypeptide causes a site-specific inversion of DNA
wherein
the inversion of the DNA is a result of recombination between the first site-specific recombination site and the second site-specific recombination site, and
wherein
the DNA that is inverted is located between the first site-specific recombination site and the second site-specific recombination site on the same DNA molecule.
8. The method of claim 1, wherein the prokaryotic Bxb1 recombinase polypeptide causes a site-specific integration of DNA
wherein
the integration of the DNA is a result of recombination between the first site-specific recombination site and the second site-specific recombination site, and
wherein
the DNA that is integrated is located between the first site-specific recombination site and the second site-specific recombination site on the same DNA molecule.
9. A method for obtaining site-specific recombination in a eukaryotic cell, the method comprising:
a. providing the eukaryotic cell
wherein
the eukaryotic cell comprises a polynucleotide that encodes a prokaryotic U153 recombinase polypeptide,
wherein
the eukaryotic cell comprises a first site-specific recombination site and a second site-specific recombination site, wherein the first site-specific recombination site is a substrate for recombination with the second site-specific recombination site; and
b. contacting the first site-specific recombination site and second site-specific recombination site with a prokaryotic U153 recombinase polypeptide, resulting in recombination between the first site-specific recombination site and second site-specific recombination sites.
10. The method of claim 9, wherein the eukaryotic cell is a plant cell.
11. The method of claim 9, wherein the eukaryotic cell is a yeast cell.
12. The method of claim 9, wherein the eukaryotic cell is an animal cell.
13. The method of claim 9, wherein the polynucleotide that encodes the prokaryotic U153 recombinase polypeptide comprises SEQ ID NO:19.
14. The method of claim 9, wherein the polynucleotide that encodes the prokaryotic U153 recombinase polypeptide encodes a recombinase polypeptide comprising SEQ ID NO:20.
15. The method of claim 9, wherein the prokaryotic U153 recombinase polypeptide causes a site-specific excision of DNA,
wherein
the excision of the DNA is a result of recombination between the first site-specific recombination site and the second site-specific recombination site, and
wherein
the DNA that is excised is located between the first site-specific recombination site and the second site-specific recombination site on the same DNA molecule.
16. The method of claim 9, wherein the prokaryotic U153 recombinase polypeptide causes a site-specific inversion of DNA,
wherein
the inversion of the DNA is a result of recombination between the first site-specific recombination site and the second site-specific recombination site, and
wherein
the DNA that is inverted is located between the first site-specific recombination site and the second site-specific recombination site on the same DNA molecule.
17. The method of claim 9, wherein the prokaryotic U153 recombinase polypeptide causes a site-specific integration of DNA,
wherein
the integration of the DNA is a result of recombination between the first site-specific recombination site and the second site-specific recombination site, and
wherein
the DNA that is integrated is located between the first site-specific recombination site and the second site-specific recombination site on the same DNA molecule.
18. A method for obtaining a eukaryotic cell having a stably integrated transgene, the method comprising:
a. introducing a first nucleic acid into a eukaryotic cell that comprises a first recombination site,
b. introducing a second nucleic acid comprising a transgene and a second recombination site, which second recombination site can serve as a substrate for recombination with the first recombination site; and
c. contacting the first and the second recombination sites with a recombinase polypeptide, wherein the recombinase polypeptide catalyzes recombination between first and second recombination sites, resulting in integration of the second nucleic acid at the first recombination site(s), thereby forming two hybrid sites flanking the inserted DNA.
19. The method of claim 18, wherein the recombinase polypeptide can mediate site-specific recombination between the first and second recombination sites, but cannot mediate recombination between the hybrid sites in the absence of an additional factor that is not present in the eukaryotic cell.
20. The method of claim 18, wherein the recombination sites and recombinase polynucleotide are selected from the group consisting of a bacteriophage Bxb1 recombination system, and a bacteriophage U153 recombination system.